WO2014195593A3 - Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant - Google Patents

Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant Download PDF

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Publication number
WO2014195593A3
WO2014195593A3 PCT/FR2014/051149 FR2014051149W WO2014195593A3 WO 2014195593 A3 WO2014195593 A3 WO 2014195593A3 FR 2014051149 W FR2014051149 W FR 2014051149W WO 2014195593 A3 WO2014195593 A3 WO 2014195593A3
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical compositions
promnesia
preparation
methods
effect
Prior art date
Application number
PCT/FR2014/051149
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English (en)
Other versions
WO2014195593A2 (fr
Inventor
Patrick Dallemagne
Christophe ROCHAIS
Cédric LECOUTEY
Michel Boulouard
Thomas FRERET
Original Assignee
Universite De Caen
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Universite De Caen filed Critical Universite De Caen
Priority to DK14806879.4T priority Critical patent/DK3004058T3/da
Priority to ES14806879T priority patent/ES2808669T3/es
Priority to PL14806879T priority patent/PL3004058T3/pl
Priority to EP14806879.4A priority patent/EP3004058B1/fr
Priority to CN201480032241.2A priority patent/CN105705488B/zh
Priority to US14/895,731 priority patent/US9663465B2/en
Priority to JP2016517648A priority patent/JP6386541B2/ja
Publication of WO2014195593A2 publication Critical patent/WO2014195593A2/fr
Publication of WO2014195593A3 publication Critical patent/WO2014195593A3/fr
Priority to HRP20201402TT priority patent/HRP20201402T1/hr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne des composés de formule (I) ainsi que leur énantiomères neurocéniques, leurs sels d'acide, leurs hydrates ou leurs produits de solvatation. Parmi un grand nombre de significations possible, X représente un halogène, Y un atome d'oxygène; tous les coefficients m,n,r et s ont la valeur 1, R représente un méthyl et R' un cycloalkyl. L'invention comprend également des procédés de préparation des composés ci-dessus et des compositions pharmaceutiques les comprenant.
PCT/FR2014/051149 2013-06-05 2014-05-19 Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant WO2014195593A2 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DK14806879.4T DK3004058T3 (da) 2013-06-05 2014-05-19 Acetylcholinesteraseinhibitorforbindelser og serotonergene 5HT4-receptoragonister med promnesia-virkning, fremgangsmåder til fremstilling deraf og farmaceutiske sammensætninger, der indeholder dem
ES14806879T ES2808669T3 (es) 2013-06-05 2014-05-19 Compuestos inhibidores de la acetilcolinesterasa y agonistas de los receptores serotoninérgicos 5HT4, con efecto paramnesiante, sus procedimientos de preparación y composiciones farmacéuticas que los contienen
PL14806879T PL3004058T3 (pl) 2013-06-05 2014-05-19 Związki-inhibitory acetylcholinesterazy i agoniści receptorów serotoninergicznych 5ht4, o działaniu propamięciowym, ich sposoby wytwarzania i zawierające je kompozycje farmaceutyczne
EP14806879.4A EP3004058B1 (fr) 2013-06-05 2014-05-19 Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant
CN201480032241.2A CN105705488B (zh) 2013-06-05 2014-05-19 乙酰胆碱酯酶抑制剂和5-羟色胺受体4激动剂的化合物，其制备方法及其药物组合物
US14/895,731 US9663465B2 (en) 2013-06-05 2014-05-19 Acetylcholinesterase inhibitors and promnesiant serotonin 5-HT4 receptor agonists, their methods of preparation and the pharmaceutical compositions containing the same
JP2016517648A JP6386541B2 (ja) 2013-06-05 2014-05-19 プロムネシア効果を有するアセチルコリンエステラーゼ抑制化合物と５ｈｔ４セロトニン作動性受容体作動薬の調製方法並びにその構成薬剤組成
HRP20201402TT HRP20201402T1 (hr) 2013-06-05 2020-09-03 Spojevi inhibitora acetilkolinsteraze i agonisti serotonergičkih receptora 5ht4, s promnezijskim učinkom, postupci za njihovu pripremu i farmaceutski pripravci koji ih sadržavaju

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1355155 2013-06-05
FR1355155A FR3006686A1 (fr) 2013-06-05 2013-06-05 Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant

Publications (2)

Publication Number Publication Date
WO2014195593A2 WO2014195593A2 (fr) 2014-12-11
WO2014195593A3 true WO2014195593A3 (fr) 2015-12-30

Family

ID=49546495

Family Applications (1)

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PCT/FR2014/051149 WO2014195593A2 (fr) 2013-06-05 2014-05-19 Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant

Country Status (13)

Country Link
US (1) US9663465B2 (fr)
EP (1) EP3004058B1 (fr)
JP (1) JP6386541B2 (fr)
CN (1) CN105705488B (fr)
DK (1) DK3004058T3 (fr)
ES (1) ES2808669T3 (fr)
FR (1) FR3006686A1 (fr)
HK (1) HK1225381A1 (fr)
HR (1) HRP20201402T1 (fr)
HU (1) HUE050953T2 (fr)
PL (1) PL3004058T3 (fr)
PT (1) PT3004058T (fr)
WO (1) WO2014195593A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2800802C2 (ru) * 2018-09-28 2023-07-28 Юниверсите Де Кан Норманди Донекоприд как нейропротекторный агент при лечении нейродегенеративных заболеваний

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3628660A1 (fr) * 2018-09-28 2020-04-01 Université de Caen Normandie Donecopride et flucopride comme agents neuroprotectifs dans le traitement des maladies neurodégéneratives
EP3952859A4 (fr) * 2019-04-12 2023-05-10 Loma Linda University Méthodes de traitement de la maladie de niemann-pick de type c
WO2023116915A1 (fr) * 2021-12-24 2023-06-29 珠海市藤栢医药有限公司 Inhibiteur double cible ache/sert, son procédé de préparation et son utilisation

Citations (1)

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Publication number Priority date Publication date Assignee Title
WO1994027965A1 (fr) * 1993-05-26 1994-12-08 Syntex (U.S.A.) Inc. Nouveaux ligands 1-phenylalcanone du recepteur de 5-ht4

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NZ243993A (en) * 1991-08-20 1994-10-26 Smithkline Beecham Plc Pharmaceutical compositions having 5-ht4 receptor antagonist activity and selected compounds having such activity
EP0774460A1 (fr) * 1994-03-30 1997-05-21 Yoshitomi Pharmaceutical Industries, Ltd. Compose d'acide benzo que et son utilisation comme medicament
JPH111472A (ja) * 1996-04-30 1999-01-06 Dainippon Pharmaceut Co Ltd ベンズアミド誘導体及びそれを含有する医薬組成物
WO1998002432A1 (fr) * 1996-07-16 1998-01-22 Takeda Chemical Industries, Ltd. Composes bicycliques pour commander la miction
IL150982A (en) 2002-07-30 2007-02-11 Ori Lerman Process for making Donafzil
US7459460B2 (en) * 2003-05-28 2008-12-02 Bristol-Myers Squibb Company Trisubstituted heteroaromatic compounds as calcium sensing receptor modulators
GB0525661D0 (en) * 2005-12-16 2006-01-25 Glaxo Group Ltd Novel compounds
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WO1994027965A1 (fr) * 1993-05-26 1994-12-08 Syntex (U.S.A.) Inc. Nouveaux ligands 1-phenylalcanone du recepteur de 5-ht4

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CÉDRIC LECOUTEY ET AL: "Synthesis of dual AChE/5-HT4 receptor multi-target directed ligands", MEDCHEMCOMM, vol. 3, no. 5, 1 January 2012 (2012-01-01), pages 627 - 634, XP055092302, ISSN: 2040-2503, DOI: 10.1039/c2md20063e *
THOMAS FRERET ET AL: "Synergistic effect of acetylcholinesterase inhibition (donepezil) and 5-HTreceptor activation (RS67333) on object recognition in mice", BEHAVIOURAL BRAIN RESEARCH, ELSEVIER, AMSTERDAM, NL, vol. 230, no. 1, 6 February 2012 (2012-02-06), pages 304 - 308, XP028472750, ISSN: 0166-4328, [retrieved on 20120214], DOI: 10.1016/J.BBR.2012.02.012 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2800802C2 (ru) * 2018-09-28 2023-07-28 Юниверсите Де Кан Норманди Донекоприд как нейропротекторный агент при лечении нейродегенеративных заболеваний

Also Published As

Publication number Publication date
US20160122300A1 (en) 2016-05-05
JP2016522215A (ja) 2016-07-28
EP3004058A2 (fr) 2016-04-13
US9663465B2 (en) 2017-05-30
FR3006686A1 (fr) 2014-12-12
JP6386541B2 (ja) 2018-09-05
HRP20201402T1 (hr) 2020-11-27
EP3004058B1 (fr) 2020-06-10
HUE050953T2 (hu) 2021-01-28
ES2808669T3 (es) 2021-03-01
CN105705488A (zh) 2016-06-22
HK1225381A1 (zh) 2017-09-08
PT3004058T (pt) 2020-09-03
PL3004058T3 (pl) 2020-11-16
DK3004058T3 (da) 2020-08-31
WO2014195593A2 (fr) 2014-12-11
CN105705488B (zh) 2020-03-24

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